December at Phoenix Sky Harbor International Airport (PHX) brings an uptick in holiday travelers bound for Chicago and other winter destinations. Expect increased TSA screening lines around mid-December and the week between Christmas and New Year. Airlines typically add extra flights or larger aircraft on the Phoenix to Chicago Midway route to match demand; Southwest is a major operator for nonstop services. For best fares and seat choice, check flexible date searches and sign up for fare alerts. If you need parking, reserve economy lots or prepay valet to reduce stress on peak travel days. Nearby connections such as Scottsdale, Tempe, Tucson, Flagstaff, and Sedona make PHX a hub for both winter sun trips and regional winter retreats.
December arrivals at Chicago Midway International Airport (MDW) require weather-aware planning. Midway is closer to Chicago's downtown than O'Hare and is well served by the CTA Orange Line for reliable transit into the city, but winter snow and ice can slow ground transport. Southwest Airlines and other carriers may adjust schedules during major storms, so check airline alerts before traveling. For visitors heading to nearby suburbs such as Naperville, Aurora, Oak Brook, or Milwaukee, plan for extra driving time and verify shuttle availability. Use live flight tracking and CTA service notices to streamline your post-arrival transfer.
December travelers flying from Phoenix Sky Harbor International Airport (PHX) can enjoy events like the Scottsdale Arabian Horse Show, holiday light displays in downtown Phoenix, and winter farmers markets in nearby Tempe and Tucson. Arrivals to Chicago Midway International Airport (MDW) offer proximity to Chicago's Christkindlmarket, ZooLights at Lincoln Park Zoo, Magnificent Mile Lights Festival, and numerous holiday theater performances in the Loop. These events increase demand for flights and hotels, so book early and consider non-peak travel days to attend popular December festivities.
For December travel from Phoenix Sky Harbor International Airport (PHX) to Chicago Midway International Airport (MDW), the best time to fly is often early morning on a weekday. Morning departures reduce the risk of weather-related knock-on delays and normally have lower fares than peak holiday evening flights. Midweek flights (Tuesday through Thursday) typically offer cheaper rates and fewer crowds than weekend travel. If you must fly during peak holiday windows, choose earlier flights from PHX to increase the likelihood of making connections and avoiding cancellations.
Nonstop flights between Phoenix Sky Harbor International Airport (PHX) and Chicago Midway International Airport (MDW) are faster and reduce the risk of missed connections during December winter weather. However, direct flights can be more expensive during peak holiday periods. Connecting flights may offer significant savings but introduce more vulnerability to weather delays at intermediate hubs like Denver or Dallas/Fort Worth. For holiday travelers prioritizing reliability, choose nonstop options when possible; budget-minded travelers willing to add time can find cheaper fares with one-stop itineraries.
Southwest Airlines often provides the most nonstop frequency between Phoenix Sky Harbor International Airport (PHX) and Chicago Midway International Airport (MDW), with flexible fare options and two free checked bags that can reduce overall travel costs for families. Other carriers may serve the route with one-stop itineraries via major hubs; these airlines may offer premium cabin options but charge for checked luggage. For December travel, compare fares including baggage fees, rebooking policies, and on-time performance metrics. Loyalty program benefits and fare flexibility can be decisive when holiday plans change due to weather.
Pack layered clothing to transition from warm Phoenix weather to cold Chicago conditions after landing at Chicago Midway International Airport (MDW). Bring essential cold-weather gear in carry-on luggage and include travel-sized hand sanitizer and face masks, especially for crowded terminals during holiday weeks. Allow extra connection time for deicing or weather delays, monitor airline notifications, and enroll in mobile alerts. Consider refundable fares or travel insurance for December trips to protect against cancellations due to winter storms.
Typical nonstop flight time between Phoenix Sky Harbor International Airport (PHX) and Chicago Midway International Airport (MDW) is about 3 hours and 45 minutes to 4 hours depending on winds and routing. In December, airlines may adjust frequencies with additional flights on peak holiday days; expect multiple daily nonstop options on carriers such as Southwest. Common connecting hubs for one-stop itineraries include Denver, Dallas/Fort Worth, and Phoenix or Chicago depending on the carrier. Check schedules early for holiday travel windows and confirm aircraft types if seat comfort matters on an overnight or redeye flight.
To find cheap December flights from Phoenix Sky Harbor International Airport (PHX) to Chicago Midway International Airport (MDW), target midweek travel (Tuesdays and Wednesdays) and be flexible with departure times. Low-cost carriers often launch holiday sales 6–10 weeks before peak dates; enable fare alerts and check incognito searches to avoid dynamic price inflation. Consider one-way searches and multi-city itineraries if your return date is flexible. For holiday weekends, book as early as possible and look for connecting flights that may lower the fare but increase travel time. Lastly, compare PHX departures with nearby airports for additional savings and monitor social media pages of major carriers for flash sales.